368447-63-6

Basic information

• Product Name: (S)-2-(aminooxy)-2-phenylethanediol
• Synonyms: (S)-2-(aminooxy)-2-phenylethanediol
• CAS NO: 368447-63-6
• Molecular Weight: 153.181
• Mol File: 368447-63-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (S)-2-(aminooxy)-2-phenylethanediol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-(aminooxy)-2-phenylethanediol(368447-63-6)
• EPA Substance Registry System: (S)-2-(aminooxy)-2-phenylethanediol(368447-63-6)

Safety Data

• Hazardous Substances Data: 368447-63-6(Hazardous Substances Data)

Upstream product

• 20780-54-5 (S)-styrene oxide 
• 405146-15-8 (1R)-2-(aminooxy)-1-phenylethanol 
• 211614-43-6 methyl (R)-(methoxymethoxy)(phenyl)ethanoate 
• 269402-51-9 (R)-2-methyloxymethoxy-2-phenyl-1-ethanol 
• 20698-91-3 (R)-methyl mandelate 
• 16355-00-3 (R)-1-phenyl-1,2-ethanediol 
• 757195-42-9 (1R)-2-{[(S)-[(2-(methoxymethoxy)phenyl)(phenyl)methyl]amino]oxy}-1-phenylethanol 
• 757195-38-3 (1R)-2-[({(1S)-1-[2-(methoxymethoxy)phenyl]-2,2-dimethylpropyl}amino)oxy]-1-phenylethanol 
• 757195-16-7 2-{[(2R)-2-(methoxymethoxy)-2-phenylethyl]oxy}-1H-isoindole-1,3(2H)-dione 
• 757195-48-5 (1R)-2-[({(1S)-1-[2-(methoxymethoxy)phenyl]ethyl}amino)oxy]-1-phenylethanol 
• 757195-34-9 (1R)-1-phenyl-2-({[(1S)-1-phenylpentyl]amino}oxy)ethanol 
• 757195-19-0 2-(methoxymethoxy)benzaldehyde O-[(2R)-2-hydroxy-2-phenylethyl]oxime 
• 757195-36-1 (1R)-2-({[(1S)-2,2-dimethyl-1-phenylpropyl]amino}oxy)ethanol 
• 757195-28-1 (1R)-2-({[(1S)-1-(2-methoxyphenyl)ethyl]amino}oxy)-1-phenylethanol 

Downstream Products

• 368447-66-9 4-methylbenzaldehyde (E)-O-[(1S)-2-hydroxy-1-phenylethyl]oxime 
• 368447-65-8 benzaldehyde (E)-O-[(1S)-2-hydroxy-1-phenylethyl]oxime 
• 368447-68-1 3-methoxybenzaldehyde (E)-O-[(1S)-2-hydroxy-1-phenylethyl]oxime 
• 368447-67-0 2-methoxybenzaldehyde (E)-O-[(1S)-2-hydroxy-1-phenylethyl]oxime 
• 502157-97-3 (2S)-2-phenyl-2-({[(1R)-1-phenyl-2-propenyl]amino}oxy)ethanol 
• 368447-75-0 (2S)-2-[({(1R)-1-[2-(methoxymethoxy)phenyl]ethyl}amino)oxy]-2-phenylethanol 
• 368447-73-8 (2S)-2-({[(1R)-1-(2-methoxyphenyl)ethyl]amino}oxy)-2-phenylethanol 
• 368447-74-9 (2S)-2-({[(1R)-1-(3-methoxyphenyl)ethyl]amino}oxy)-2-phenylethanol 
• 368447-76-1 (2S)-2-[({(1R)-1-[3-(methylsulfanyl)phenyl]ethyl}amino)oxy]-2-phenylethanol 
• 368447-72-7 (2S)-2-({[(1R)-1-(4-methylphenyl)ethyl]amino}oxy)-2-phenylethanol 
• 368447-64-7 3-methoxybenzaldehyde O-[(1S)-2-methoxy-1-phenylethyl]oxime 
• 368447-71-6 (2S)-2-phenyl-2-({[(1R)-1-phenylethyl]amino}oxy)ethanol 
• 25779-13-9 (S)-1-phenyl-1,2-ethanediol 
• 757195-24-7 (2S)-2-({[(R)-[2-(methoxymethoxy)phenyl](phenyl)methyl]amino}oxy)-2-phenylethanol 

Relevant articles and documents

Ring-Strain-Enabled Catalytic Asymmetric Umpolung C-O Bond-Forming Reactions of 1,2-Oxazetidines for the Synthesis of Functionalized Chiral Ethers

An unprecedented catalytic asymmetric umpolung C-O bond-forming reaction of N-nosyl 1,2-oxazetidines with β-keto esters has been achieved in the presence of a chiral phase-transfer catalyst, allowing access to a range of highly functionalized chiral ethers bearing quaternary and no adjacent stereogenic centers with high yields, excellent enantioselectivities, and diastereoselectivities (up to 97percent ee and 20:1 dr). These versatile products could be flexibly transformed into biologically important chiral fused and spiro morpholines in two steps.

Nucleophilic addition of methyllithium to chiral oxime ethers: Asymmetric preparation of 1-(aryl)ethylamines and application to a synthesis of calcimimetics (+)-NPS R-568 and its thio analogue

Chiral (E)-arylaldehyde oxime ethers, prepared using (R)-1-phenyl-1,2-ethanediol as a chiral auxiliary, undergo nucleophilic addition with methyllithium to give diastereomerically enriched O-alkyl hydroxylamines which, after reductive N-O bond cleavage, lead to the corresponding (R)-1-(aryl)ethylamines. This methodology has been applied to the enantioselective synthesis of a new type of arylalkylamine calcimimetics (R)-(+)-NPS R-568 and its thio analogue.